(2S,6S,7R,10R)-2-(2-Benzyloxy-ethyl)-10-hydroxy-3-methyl-12-oxa-tricyclo[5.3.2.0^1,6]dodec-3-en-11-one

Base Information

• Chemical Name: (2S,6S,7R,10R)-2-(2-Benzyloxy-ethyl)-10-hydroxy-3-methyl-12-oxa-tricyclo[5.3.2.0^1,6]dodec-3-en-11-one
• CAS No.: 72844-65-6
• Molecular Formula: C₂₁H₂₆O₄
• Molecular Weight: 342.435

Synonyms:(2S,6S,7R,10R)-2-(2-Benzyloxy-ethyl)-10-hydroxy-3-methyl-12-oxa-tricyclo[5.3.2.0^1,6]dodec-3-en-11-one

Chemical Property of (2S,6S,7R,10R)-2-(2-Benzyloxy-ethyl)-10-hydroxy-3-methyl-12-oxa-tricyclo[5.3.2.0^1,6]dodec-3-en-11-one

Chemical Property:

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Technology Process of (2S,6S,7R,10R)-2-(2-Benzyloxy-ethyl)-10-hydroxy-3-methyl-12-oxa-tricyclo[5.3.2.0^1,6]dodec-3-en-11-one

There total 3 articles about (2S,6S,7R,10R)-2-(2-Benzyloxy-ethyl)-10-hydroxy-3-methyl-12-oxa-tricyclo[5.3.2.0^1,6]dodec-3-en-11-one which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

(4aS,5R,8aR)-5-(2-Benzyloxy-ethyl)-6-methyl-1,4-dioxo-1,3,4,5,8,8a-hexahydro-2H-naphthalene-4a-carboxylic acid methyl ester (72844-64-5) → (2S,6S,7R,10R)-2-(2-Benzyloxy-ethyl)-10-hydroxy-3-methyl-12-oxa-tricyclo[5.3.2.01,6]dodec-3-en-11-one (72844-65-6)

Guidance literature:

With L-Selectride; In tetrahydrofuran; at -78 - -25 ℃; for 12h;

DOI:10.1021/jo01294a058

Reference yield:

6-Benzyloxy-3-methyl-1,3-hexadiene (138703-08-9) → (2S,6S,7R,10R)-2-(2-Benzyloxy-ethyl)-10-hydroxy-3-methyl-12-oxa-tricyclo[5.3.2.01,6]dodec-3-en-11-one (72844-65-6)

Guidance literature:

Multi-step reaction with 3 steps

1: 95 percent / Ag₂O / benzene

2: 1) Zn/HOAc; 2) Al₂O₃

3: L-Selectride / tetrahydrofuran / 12 h / -78 - -25 °C

With aluminum oxide; L-Selectride; acetic acid; silver(l) oxide; zinc; In tetrahydrofuran; benzene;

DOI:10.1021/jo01294a058

Reference yield:

(4aS,5R,8aS)-5-(2-Benzyloxy-ethyl)-6-methyl-1,4-dioxo-1,5,8,8a-tetrahydro-4H-naphthalene-4a-carboxylic acid methyl ester (72826-90-5) → (2S,6S,7R,10R)-2-(2-Benzyloxy-ethyl)-10-hydroxy-3-methyl-12-oxa-tricyclo[5.3.2.01,6]dodec-3-en-11-one (72844-65-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 1) Zn/HOAc; 2) Al₂O₃

2: L-Selectride / tetrahydrofuran / 12 h / -78 - -25 °C

With aluminum oxide; L-Selectride; acetic acid; zinc; In tetrahydrofuran;

DOI:10.1021/jo01294a058

upstream raw materials:

(4aS,5R,8aR)-5-(2-Benzyloxy-ethyl)-6-methyl-1,4-dioxo-1,3,4,5,8,8a-hexahydro-2H-naphthalene-4a-carboxylic acid methyl ester

6-Benzyloxy-3-methyl-1,3-hexadiene

(4aS,5R,8aS)-5-(2-Benzyloxy-ethyl)-6-methyl-1,4-dioxo-1,5,8,8a-tetrahydro-4H-naphthalene-4a-carboxylic acid methyl ester

Downstream raw materials:

(1R,4R,4aS,5S,8aS)-5-(2-Benzyloxy-ethyl)-4a-hydroxymethyl-6-methyl-4-(tetrahydro-pyran-2-yloxy)-1,2,3,4,4a,5,8,8a-octahydro-naphthalen-1-ol

C₂₅H₃₂O₇

(2S,5S,6R,9R,12S)-12-(2-Benzyloxy-ethyl)-9-methyl-10-oxa-tricyclo[7.2.1.0^1,6]dodec-7-ene-2,5-diol

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